


Best Buds

by NetflixandCastiellll



Category: Supernatural
Genre: Dean Angst, Dean Fluff, Dean Smut, Dean Winchester Angst, Dean Winchester Fluff, Dean Winchester Smut, F/M, Supernatural smut
Language: English
Status: Completed
Published: 2016-03-25
Updated: 2016-04-09
Packaged: 2018-05-28 21:54:46
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 7
Words: 20,792
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6346903
Author URL: https://archiveofourown.org/users/NetflixandCastiellll/pseuds/NetflixandCastiellll
Summary: <blockquote class="userstuff">
              <p>Dean has been your best friend for years. Will these drunken times lead to something more? Or will it make living in the bunker and going on hunts awkward for everyone?</p>
            </blockquote>





	1. Part One

You had met the Winchesters after they had saved you from a nest of vampires that were attacking your school. The leader had you pressed up against the wall with his teeth an inch away for piercing the tight skin on your neck when they burst into the library.

“Sammy!” The taller one, who you assumed must be Sammy, gracefully tossed a machete to the assertive one. It looked like a choreograph dance, the way the two attacked the vampires that were fighting back. You almost forgot you were pinned between a wall and a monster while your eyes trailed each of their movements. The towering man was in the middle of slicing off two heads when suddenly you were dropped to the floor and the vampire was ripped away from you. You must have hit your head against the wall because your vision became burry and you felt your mind slipping away. The last thing you remember before passing out was looking up into emerald eyes and sold arms picking you up.

* * *

Ten years had passed since then and you hadn’t left the brothers side. Your family was killed by those vampires and you fell into the hunter life soon after. Sam and Dean took you in and let you live in their bunker. The three of you became inseparable and it felt like having family again. Going on hunts and spending off time together was your whole life. Dean trained you in obstacle courses and built up your strength while Sam taught you everything he knew about monsters and how to kill them. Sam was a great friend, supportive and caring. The two of you were very close, but your relationship with Dean was on another level.  You had never grown to trust another human being as much as you trusted Dean Winchester. Maybe it was because he was the one to save you. Or maybe it was because he never let you down.  But when it came down to it, you didn’t care why you trust him; you just knew that you could. He was your best friend and you didn’t know what you would do without him. Sam often joked around saying that the two of you were perfect for each other but the both of you laughed and brushed it off, knowing that it was just friendship.

* * *

“Ay, Sammy, (Y/N) and I are goin’ out for some drinks and pool. Wanna come?”

“No, I’m actually about to head out to Bobby’s in a few. He needs help doin’ research on a case he found out in Idaho.” Sam smiles up at his older brother while packing up a bunch of books and his laptop into a duffel bag.

“Got it. Call when you get back.” Dean rolls his eyes and slaps his brother on the back then struts off to his room.

Sam looks over to you sitting at the table flipping through some lore on Wendigos. “Hey, (Y/N)… you cool being Dean’s wingman for the night? It’s been awhile since the guy has gotten lucky!” He laughs and grabs his stomach. “And trust me, he needs to soon. Can’t you tell he’s getting grumpy?”

“Sam, I am a freakin’ Jedi Master at being a wingman. You got nothing to worry about. If anyone can get Dean laid, it’ll be me.”

When you were getting ready for the night, you decided that you weren’t going to be left hanging. You needed to blow off steam as well. There was no way in hell that Dean Winchester would be the only one getting laid tonight. So you put on your favorite dress that gave you amazing cleavage and hugged your curves perfectly.  You curled up your hair and grabbed some high heels.

“(Y/N)!! You ready?!” Dean shouted down the hall, eager to get some liquid courage into his blood stream. “Let’s get goin’! First round on me…”

You bumped into him while you were running out of your room, smearing on some lipstick. “Ha! Your money is comin’ from the same place mine is dork!” Dean grumbled in response and grabbed your elbow. “Okay! Okay! Let’s go! Let me just put on my shoes…Did you remember to bring your jacket, Dean?”

Tugging you towards the door, “Uhhhg… Yes, Mom…”

“What the fuck did you just call me?” You yanked your arm away from him and there was steam practically coming out of your ears. Your eyes were piercing into the now scared expression on Dean’s face. You hated it when the boys called you mom. They just meant it as a term of endearment, but it made you feel weak, overbearing and anything but sexy. You’d made it very clear in the past that you hated it and it had been a long time since that they had called you that.

“Crap… I didn’t mean it like that, (Y/N)… Sorry.” He knew he fucked up. The way he was looking at you meant he was anticipating a slap in the face.

“Whatever. Let’s go.”

When you got to the dive, you marched straight up the bar and ordered two doubles. Dean thought one was for him, but when he saw you down both of them within seconds, he knew you were still mad.

“Hey, uh Dimitri, two more over here.” Dean slid one over to you and watched you gulp it down with ease. His eyes never left you when he sipped his slowly. “(Y/N)…”

“Keep ‘em comin’, D…” You wave two fingers over to the bartender and he winks back at you.

“(Y/N)… I’m sorry. I didn’t mean it.”

“Forget it Dean. It’s fine. Now come on, let’s find some poor girl for the night. What about that one?” You point over to the busty blonde leaned up against the jukebox. Dean gives you a small nod and takes another sip. Smiling to yourself, you get up and stumble slightly out of your chair. The girl is pushing in a nickel and flipping through the music when you walk up behind her.

“H-hey! Nice s-shoes… where’d you get ‘em?”

“Uh thanks! Um some random store in the city…”

“Pickins are slim tonight aren’t they? Only one guy worth the effort and he’s playing’ hard to get.”

She chuckles and waves to Dean who was now staring at the both of you. “Strike out huh? I saw you talking to him earlier.”

“Hmm. Not really… just givin’ him the taste of his own game. I’ll have that one wrapped around my finger before he knows it.”

“Ha! Night’s not over sweetie, I’ll be damned if I let you take the only fuckable guy in here.” The blonde flips her hair as she swings her body to turn around and swagger over to Dean.  You smile to yourself from another successful play. You raise your glass towards Dean and he winks at you in thanks.

The amber liquid slides down your throat and you push a nickel into the box. AC/DC starts ringing through the bar and you let it wash over you. The sway of your hips moves in sync with the music and you close your eyes to revel in the floating feeling this whiskey is giving you.

“Well hey there, pretty lady. Name’s Daniel.” When you stop dancing and open your eyes, a large hand is in front of you waiting for your return gesture. Your vision is a little blurry but you can make out the tall figure with perfectly combed blonde hair wearing a navy pinstriped suit. “Whatta you say you give me a little dance?” He smiles down at you and his hand brushes your hip.

“Buy me a drink first, buddy.” You scoff, walk off to the bar, sit on the wooden stool and push your empty glass to the edge. Turning to your right, you see Dean and the blonde chatting away. She throws her head back and laughs while she grabs Dean’s arm. Your view becomes obstructed when Daniel sits down on the next stool over. He signals over to the bartender.

“Double for me and uh vodka cran for the lady…” He clicks his tongue and winks at you.

_Uhg gag me…This poor guy has no chance._ “Uh no thanks. I’m good.” You roll your eyes and tap your empty glass on the table. The bartender pours you another double and you sip it with a smirk.

Daniel chuckles under his breath. “Hmm, looks like I’m in over my head. Look, I didn’t mean to offend. I just wanted to buy you a drink and chat.”

Maybe it was the cheap whiskey or maybe it was from you being so god damn horny, but you decided to give the guy another chance. He was drop dead gorgeous after all. It ended up you were glad you did. Turns out Daniel grew up the town next to the one you had and you had a few things in common. The two of your talked for what seemed like hours and he made you laugh uncontrollably. Every time your glass was half an inch form being empty, he filled it back up to the brim. He was trying to get you drunk and it was working. Your words were slurring and your hand touching his arm you felt like you were floating above ground. You noticed that Dean kept glancing over at you instead of paying attention to the girl in front of him. He looked furious. Every time Daniel’s hand moved to touch your thigh, Dean gulped down a shot.

“How about we get outta here and have some fun?” Daniel pours you another one but you know I’ve already almost reached your limit. One more drink and you’d wake up God knows where.

“S-sure thing! Let’s go. I’ve gotta room at the motel across the street. Um… L-let me just let my friend know I’m headin’ out.” Not seconds later, Dean’s arm is wrapped around your shoulders. He gives you a little squeeze and smiles over to Daniel.

“Hey man! Thanks for keepin’ my girl company while I was gone.”

“S-what the fu-?” You look up to him pissed and confused.

“Come on honey. Time to go home.” Dean grabs you by the wrist and drags you of the chair, pulling you out the door. When you try to pull away, he picks you up and throws you over his shoulder. “You’re wasted. Let’s go. There’s no way you’re going anywhere with that douche bag.”

“D-dean! Stop! P-put me d-down!” You were so drunk you couldn’t control your muscles like you wanted to, so struggling against Dean’s grip was pointless. He tossed you into the front seat of the Baby and slammed the door shut. When he climbed into the driver’s side, he reached over and buckled your seat belt. You huffed and shrugged him off and leaned up against the window.

“You’re welcome.” He scoffed.

“Welcome?! W-welcome for what?! For c-cock blockin’ me? For preventin’ me from getting fucking laid? Uhg God damn it Dean! You aren’t the only one that n-needs to get laid round here….” Dean didn’t respond. He just shifted in his seat slightly after turning on the engine. He drove straight past the motel the two of you were staying at and sped down the road. “Uh hello?! You passed the motel…” Waving your hand in front of his face, he is still ignoring you. You felt yourself getting dizzy and loosing control over the filter of the words coming out of your mouth. “Wh-what-tever. Fuck. Now I’m h-horny as hell and got no one to fuck round with.  And getting myself off hasn’t d-done the trick lately.”

You notice Dean shift around in his seat again and he tugged at the hem of his shirt, pulling it so it covered part of his lap. You burst out into laughter. “Oh my God! Ha! You’ve got to be kidding me. You’ve got a hard on, don’t you?” He still doesn’t say anything. Eyes focused on the road, but he starts to speed up. You felt flushed and warm from the liquid courage running through your bloodstream mixed with the anger you had towards him. Something came over you; shrugging to yourself, you reach over and start to palm Dean’s half hard cock through his jeans. He jumps from the surprise sensations and the Impala swerves off the road and back on quickly after. He slams on the breaks and backs away from you.

“What the hell!? Stop! You’re drunk…”

You grumble and roll your eyes. “R-elax-ax, Dean. D-don’t act like you ha-haven’t thought about this b-before. The bunker has thin wa-walls…besides, you owe me this one, blue beaning me and all.”

Dean starts up the car again and pulls onto the road. “I’m not letting you do this. I ain’t takin’ advantage.” But when you kiss him, he doesn’t stop you. Instead he deepens the kiss and pushes in tongue inside, exploring your mouth. “(Y/N)…we shouldn’t…” You reach over and start unbuckling his pants. He presses his foot harder into the pedal when you pull out his length and give it a few pumps.

“Slow down, D-dean. Don’t want to get pulled over for speeding and ruin the f-fun.”

You unbuckle your seatbelt and slide over closer to him. Leaning down you rub the tip of his head and smear leaking precum along his shaft making him slick and soft. You lick your lips in response, wondering what he might taste like. It wasn’t like you hadn’t seen your best friend naked before. You’ve patched up more wounds of his than you could count. You even walked in on him masturbating one time when he forgot to lock his door. But this was different. Seeing him exposed in front of you, for you, was overwhelming. You were dizzy enough as it is and feeling his throbbing cock between your fingers took you to a whole other level. Dean let out a loud gasp when you wrapped your lips around the head of his prick. His fingers threaded through your hair and he massaged your scalp. His breathing became sporadic and he was pushing your head down further while he pushed shallow thrusts up into your mouth. You pulled off with a pop and gave him a smirk.

“If you think I’m d-doing this for you…you are ma-mistak-ken. Pull over. You’re gunna to lay me down in the back seat and fucking eat me out til I don’t even know my name anymore.”

Dean turns the car into an empty patch on the side of the road. You both climb over to the back seat and start to strip down your clothes. You are soaking with your arousal and you start touching yourself before Dean even has all of his clothes off. Dean keels on the floor while you lay out over the seat. He grabs your legs and pulls them over his shoulders before he dives in. The adrenaline had sped up your heartbeat and alcohol in your bloodstream was hitting you faster. You were wobbly and giddy and when his tongue grazed over your clit and you pressed your thighs together.

“Holy shit! You sure are livin’ up to your reputation, Winchester…ohh fuck.” Pulling on his hair, you arch up into his face grinding your hips to get more friction. He pushes his tongue firmly against your clit. Two long fingers slide into you while plump lips wrap around your clit and suck. He starts pumping into you fast with curled fingers, massaging your gspot with precision. You are getting closer to your peak and you clench around his fingers. Dean gets the message and starts sucking and licking harder. His fingers are scissoring, pumping and flicking around, exploring every inch of you. “Ohhh shit, Dean! Yes!” You cum hard around his fingers and thrash around but his strong hands are pinning you down. He slurps and gulps up the juices leaking out and he doesn’t slow down for one second while your body convulses against his face.

“Mmm… fuck, (Y/N). You taste amazing.” He sits up and licks his lips that are covered in your slick. He moved over you to kiss you, but you push him away.

“L-like I said… Th-this was for me…” You sit back up and pull your dress back on, not bothering to put on your bra. You climb back over to the front seat and buckle back up.

Dean huffs and follows suit. He pulls up his pants, leaving off his shirt and climbs over the seat. You pass out on the drive back home and when you arrive, Dean carries you inside. Sam is still working with Bobby in Idaho so the bunker is still empty. Your best friend lays you out on you bed and you groan and roll over, grabbing your head.

“Shhh… shhh… it’s okay. Go to back to sleep. I got you…” Dean leaves the room for a few minutes and comes back with some clothes, aspirin and a glass of water. When he sits you up, you loose your balance and fall forward onto his chest. “Alright. I gotcha…” He lifts you back up and pulls your dress over your head. Then he slips you into one of his old band t-shirts and oversized flannel pajama pants. Dean gets you under the covers and tucks you in and when he attempts to kiss you on the forehead goodnight, you pull him down into a sloppy wet kiss on the lips, drunkenly so that you knock your forehead against his. “Okay… there tough shot, time to sleep.”

“N-no… wh-wait, De-an… don’t… wait. I HAVE to tell you s-somethin’.” You try to sit up but end up falling on your side. “Ya-you my friend… give the best… uh wh-what’s the other v-ersion of of of g-ivin’ head?” You cackle and then fall back onto the pillow, passing out once again.

Dean smiles to himself and shuts off the light, “Good night, (Y/N). See ya in the morning.”


	2. Part Two

**Summary for the Chapter:**

> Dean has been your best friend for years. Will these drunken times lead to something more? Or will it make living in the bunker and going on hunts awkward for everyone?

The echoing of a coffee grinder startles you awake the following morning. “Uhg! What the fuck is that noise?” You pull the pillow over your head and wrap yourself tighter into the blanket. Your head is ringing and pounding from one of the worst hangovers you have ever experienced. Clenching your eyes tighter, you wish Castiel could pop over and heal you up. Pieces of memories from last night start to cloud your head and you groan. The flash of an imagine of you dancing with some blonde on top of a table makes you cringe and when you pucker your lips from regret, the taste of cheap whiskey lingers. Suddenly the light in your room flicks on and you let out another groan and curl up into a ball.

“Good morning, sleepy head!” The other side of the bed slumps and you hear clanging of mugs being placed onto the bedside table, but it sounds like a war zone. The blankets are tugged off of you and you cover your eyes with your hands to prevent the light from stinging your brain. “Come on! Time to get up! I got hot coffee for ya here.”

“Go away, Dean. I’m hungover.” You try to pull back the blanket but he tosses it across the room.

“Best cure for that is a hot cup of coffee and greasy food!” He smiles and pushes a mug into your hands.

“I want to puke at the thought of food. Why did you let me drink that much? What the hell happened last night?” You sit up and take a sip of the steaming coffee. It burned all the way down but it felt like a cleanse of your soul. “L-last thing I remember, I was playing rock, paper, scissors with that guy, uh… Da…Don… Danny or something…”

Dean’s comforting smile fades away and he frowns slightly. “You don’t remember?” He picks up his cup and takes a few gulps. You start to massage your temples to release the tension while you try to sort through what happened.  

“I-I… um not really. Could you give me a play by play?”

Dean fiddles with his fingers and adjusts his posture. “Just a typical night. You had a lot to drink. Danced to AC/DC and we made last call. Then I took ya home and put you to bed.”

“You mean you didn’t take that blonde to the motel?” Pushing your eyebrows together in a confused look, you touch his shoulder. He flinches at your touch and you quickly retract your hand back.

“Nah… Sometimes you gotta reel ‘em in and then let ‘em go. Keeps the game fun.”

“Oh.” The only sound left in the room is the ticking of the wall clock and the tapping of your fingers on the now empty mug. There was an awkward tension in the air and you couldn’t place your finger on why. Dean looked uncomfortable and his eyes were shifting, probably looking for an excuse to leave the room. “Thanks for the coffee.” You give him a smile and then climb out of bed to pick up the blanket. “Just ten more minutes… please?”

“Alright.” Dean turns and kisses you on the temple of your head and like a light bulb went off in your head, everything that had happened in the Impala came rushing back. The taste of him. The soft sounds he made when your lips touched the sensitive parts of his body. His fingers on your skin. The feeling of his tongue and fingers exploring every inch of yours. The wave of realization hit you like a brick.

“Shit. Dean. I-I remember.” You bury your face into your hands and scrunch your hair between your fingers. “I can’t believe I did that to you. Oh God. I am so sorry. I’m fucked up for taking advantage of you like that. Crap… Crap… I didn’t mean to put you in that situation. I’m a shit friend… ahh God. I’ve ruined everything… We had a good thing going and I fucked it up.”

“(Y/N)! (Y/N)…” He gentlly shakes your shouders. “Shhh…shhh. It’s okay… There were two people in this. It‘s just as much my fault as it is yours. I wasn’t as drunk ‘nd I easily coulda stopped you but I didn’t.” He lifts up your face with his finger under your chin and then wipes away a tear. “Look… it was a drunken mistake. Neither of us were the right mindset. We forget this ever happened and move on like normal.”

“But… but what if Sam…”

“Sammy won’t know shit. Relax. Play it cool and it’ll be fine. We’ll do this together.”

You wish you could say everything was fine after that night, but you’d be lying. It affected research, hunts and everyday life. You could barely look Dean in the eye let alone work with him on a hunt. When you guys bumped each other, you’d pull away quickly and act like it didn’t happen. When you needed help or needed to ask a question, you turned to Sam. Dean wanted to say things to you all the time but as soon as his lips parted, you’d turn and walk away. After a quick hunt involving a werewolf, Sam left to pick up dinner for the night leaving the two of you alone in the bunker.

“Um hey, I think I’m just gunna shower and then go to bed. I’m not hungry.” You rub the back of your neck and pick off a pieces of dirt left on your clothes.

Dean let out a heavy sigh and planted his hands on the table. His eyes closed tightly and hands beginning to fist. “No.”

“What?”

“I said no.”

“Dean. Wh-”

He roughly slid his hands across the table, making books and loose paper fly across the room. “Damn it, (Y/N)…I’m sick of this… I said it would be okay and it’s not. You’re ignoring me! You won’t even look me in the eye! What the fuck did I do? I thought our friendship was strong enough to get pass this shit! Guess I was wrong.”

“Dean, I’m so-”

“Forget it.”

“No wait, Dean! I’m sorry! I am! I don’t know why I-I shut you out. I-I think I was scared.”

“Scared? Scared of what?” He was yelling. It made you cringe because you rarely saw Dean yell unless he was hunting.

You spat words back. “Of losing you! You’re my best friend, Dean! And I fucked everything up! Distancing myself…pushing you away…it was easier than you telling me you didn’t want me around anymore. I could deal with myself making the choice, but not from hearing that from you.“

Dean walked over and cupped your face into his hands. You were surprise at how much you relaxed to his touch. You melted into his hands. You missed it. You missed him. ”(Y/N)… I already told you that we are in this together. We both made that mistake. We both need to clean it up. Together.“You fell forward onto his chest and began to cry. All of the sorrow, fear and regret was being let out and Dean was carrying you though it all. He hugged you tight and stroked your head. "We can get over this. We’ll be fine.”

Everything fell into place after that. You truly believed that Dean was in this with you. And after a couple days it felt like old times. Jokes, music and food filled the empty hole in your souls. The two of you were chowing down burgers and Sam was munching away at a salad. After dinner you and Dean were ganging up on Sammy, teasing him that you caught him humming Taylor Swift while he was cooking. You were laughing together and finishing each other’s sentences.

“What the hell happened” Sam eyed back and forth between you and Dean.

“Whatta you mean, Sammy?”

“Y’ll are talking again… Don’t act like I didn’t notice how awkward it’s been the last week.” He chuckles and swirls the whiskey in his glass.

“Nothin’.” Dean says it quickly and quietly.

“We had a little miscommunication. But we’re good now.” You give Dean a small smile.

Sam scoffs and rolls his eyes. “Okay. Whatever you guys say…. Alright I’m out. I gotta at least try and get some sleep.”   
  
“Bitch.”

“Jerk.”

You couldn’t help but laugh at their bickering. It finally felt right again. Letting out an exhausted sigh, “Right behind ya, Sam! I’m pooped. I’ve got a food baby.” You rub your belly and laugh. “Thanks again for dinner, Sam.”

You climb into bed and let out a few deep elongated sighs. It’s the first real night’s rest you’d gotten in a long time. The stress with Dean was lifted off of your shoulders and you felt happy again. You were sung in your pillows and wrapped tight inside your blanket when you heard something strange. Muffled and coarse. There was silence for a few seconds and then a sharp cry. You pull the gun from underneath your pillow and jump out of bed, landing on the floor without a sound and you thank Cas the floorboards aren’t creaking. You peel open the bedroom door and slip out into the hallway. The sounds start up again and gets louder with each step you take. Light is spilling out from underneath Dean’s bedroom door and you hear a thud. You tip toe to stand in front of his room and see that the door is ajar.

You attempt at a whisper but it comes out louder than you expected. “Dean?… Dean?!” There is no answer but you hear another thud. You push open the door and his room is empty. Steam is bustling out from the bottom of the bathroom door and you hear the shower. You let out a relieved sigh to realize that there is no sight of any demons or monsters. _Not much can get through those doors. This place is warded from everything. Uhg duh. I’m going back to bed._ Turning on your heels, you move to go back to your bed, when you hear it. It’s muffled and soft but you are sure of it. The sound of your name escaping his mouth is one that is burned into your memory. The closer you move to the bathroom door, the louder the moans, cries and groans fill your ears. You are pressed up against the door with your eyes closed and a rush of heat consumes your body. Taking in every breath, every letter that leaves his lips. You push the door open more to get a better view. His scent fills you up and it makes you dizzy.

“(Y/N)…. Mmm, (Y/N)….fuck…”

The sight of Dean Winchester pumping his swollen cock through the steamy glass door, meets your eyes. _Fuck. Again? I thought…but he said…_ You couldn’t tear your eyes away from his body. The whole sight was moving in slow motion and every sound was prominent. His stiff muscles were contracting with each stroke. You felt like you could hear the water droplets traveling down his chest and arms. The flutter of his eyelashes in rhythm with his heartbeat. Your arousal was overwhelming your thoughts and all you wanted to do was to burst into the shower and let him take you however he wanted. You could feel yourself soaking below and you began to shake from nerves. Your name leaked his lips again and you were done for. _Crap… I can’t be here. I can’t take this._ So you move out of the room quietly, closing the doors behind you. 

When you got back into your room, you were on the verge of hyperventilating. You paced in circles around the room and threw your hands to your head. Shaking your head ‘no’, you try and collect yourself. _I can’t believe he is still doing this. After all this shit that has happened…fuck!_ Your brain kept telling you to let it go and head back to sleep. However your hormones, at least you told yourself that, were in control. You remove your clothes like they are on fire and climbed onto your bed. The slick from your thoughts was dripping down your thighs. Letting out a few whimpers, you were surprised at how eager and sensitive your body was to reacting to your own touch.  Your fingertips caress your soft skin and goose bumps arise with every graze. Dean’s hands are much rougher than your own and you wish you could feel his calloused hands massage your breasts and pinch your hardening nipples. You use your nails to tickle a trail down to your hot aching center and then draw lines and circles at the apex of your thighs. Sliding two fingers between your wet folds, your thighs instinctively press together. Teasing your begging center for what it really needs, you touch yourself everywhere except where you want it most. When you finally let yourself touch your delicate clit, you arch your back and let your free hand grip the headboard. Gasping in air and then biting your tongue to hide your cries, you pull the blanket over to stuff some into your mouth. You bite down on the fabric and let it silence your moans. As you are getting closer to peak, your thoughts lose control once again and streaks of images of Dean looking up at you while his tongue works its magic engulfs your attention.

“Ohhh fuck, yes… Dean… please…” A spark ignites your body and you let go.

Unexpectedly, you jolt awake. You sit up and rub your eyes with the palms of your hands and let out a yawn. It takes a second for the dream to settle in, but then your eyes widen and your jaw drops. _Shit._

A knock on the door.  “(Y/N)? You okay in there?”


	3. Part Three

**Summary for the Chapter:**

> Dean has been your best friend for years. Will these drunken times lead to something more? Or will it make living in the bunker and going on hunts awkward for everyone?

_Knock. Knock._ “(Y/N)?” _Knock. Knock._ “It’s past one. You awake? You never sleep in this late.” Sam’s smooth voice was comforting to your dumbfounded thoughts.

“Yea. Yea… I’m fine, Sammy. Shit. Sorry, I’ll be out in a minute.” You stretched out your arms and legs and then climbed out of bed to get ready for the day. You noticed you had kicked off your shorts and underwear in your sleep. _Uhg. This can’t be happening._ When you got into the kitchen, lunch was already made and you figured your portion was already cold. You made a mental note to apologize again to Sam. As you bit into your burnt toast and chugged down the cold black coffee, you let your dream replay over and over again. _How could I let this happen? There is no way I am into Dean Winchester. No. No way. I’m just horny… geez I need to get laid._ No one had found any cases recently and the demon activity was quiet since Crowley came back into power. You might have hated the guy but he did keep a tight ship in Hell.

Dean walked into the kitchen wearing his dead guy robe, carrying an empty mug. He walked straight to the coffee pot and carried it over to table. He fills up your cup before refilling his own. When he sits down next to you, he picks up your half eaten toast and takes out a bite. “Hey there, bubs. Get a good night’s rest?” You grumble in response. “Guess not… So Sammy is gunna to be workin’ out all day and I already gave Baby a bath. You got any plans today?”

“No… I guess I could just catch up on some sleep, maybe pick up groceries.”

“Alright. Well you wanna watch a movie later? I’m thinkin’ Star Wars marathon!”

You wanted nothing more than to spend time with your best friend. Cuddle up and have a movie marathon but you were worried you had become too attached. Attached beyond the point of friendship. You didn’t want to ruin things more than you had already and with this dream, you didn’t know what you might end up doing. _Maybe I can just tell him that I’m not feeling good._  “Um… I don’t know. Maybe. I’m actually not feeling too good. I’ve got a headache.”

“Come on! You fuckin’ love Star Wars!” He gave you a light punch on the shoulder.

“Dean…”

“Get in some sweats and meet me in my room.” He was exceedingly insistent. A big grin was taking over his face, stretching from ear to ear. You always loved the crow’s feet that appeared in the corners of his eyes whenever he smiled or laughed. You gave up in trying to convince him to let you go back to sleep since you figured he’d end up watching the movies in your room to spite you.

Dean practically danced his way into his room with the movies in hand. You were in your favorite pair of sweatpants and one of Sam’s old flannels that you refused to let him throw out. He popped in A New Hope, which was both of your favorites and then plopped a bowl of popcorn in your lap. Then he passed you a glass of water and two aspirin. “Don’t worry. These’ll kick in ‘nd you’ll feel better in no time.” He patted the back of your head and then sat down next to you, propped up against the headboard. It was a little awkward at first, your hands kept touching when you reached for popcorn and it made you nervously sweat. Dean wasn’t fazed for one second. He casually watched the movie and quoted lines constantly. He tossed a couple piece of popcorn in the air and caught them just in time with his mouth. He wasn’t normally this clueless but at some point he must have began to notice. You were awfully quiet and didn’t even make a sound when your favorite scenes happened. He nudged your leg and then threw a few pieces at you face, shaking you back out of your thoughts. Your reaction made him huddle over and grab his stomach while he laughed.

“What’s wrong, party pooper?”

You roll your eyes at the childish remark. “Nothin’. I guess I’m just tired.”

“Alright.” He patted his shoulder that faced you as an invitation for you to lean up against him. You hesitated, so he snaked his arm around your shoulders and pulled you in tight. Your head fit like a glove touching his shoulder and you let out a relieved sigh when you finally relaxed into him. Dean may be sturdy and broad shouldered but he was comfortable. You felt yourself being lulled to sleep despite the loud battle sounds that were currently coming off of the tv. So you adjusted your body so that you could spread out and rest your head on his chest and lap. Your head rose up and down from his breathing and you began to drift to sleep. As soon as your eyes shut, you felt something press against your cheek. _It’s probably just the fly of his jeans._ You adjusted your body again and moved your arms to rise above your head to cushion your face slightly, crossing Dean’s legs. When you nuzzled your face into your arms, you felt it again except more noticeably. It was hard and warm, grazing the side of your face. Dean’s body quickly tensed, so you sat up. His hands moved quickly to cover his tented jeans. You looked him dead in the eye and noticed that the green was faded away. His face became flushed and red from embarrassment.

“Crap. I’m fuckin’ sorry, (Y/N).”

“Dean…”

“It’s just your face ‘nd it was there ‘nd ahhg fuck…” He covered his face with his hands and moved his legs off of the bed, turning away from you.

“Dean, it’s fine… I uhh I guess I should take it as a compliment… right?” You move to sit on the side of the bed with him and place a hand on his back. “I guess it’s to be expected. I mean after that night… There’s no real goin’ back from that, is there? We are fuckin’ kidding ourselves.”  
“I heard you…” It came out like word vomit.

“What?” You pulled your hand away from rubbing alleviation on his back.

“I heard you… walls are thin… remember?” He turned his head to the side to face you.

“Shit.”

“I heard you say my name…’nd after that… I-I couldn’t help myself. I went in the shower ‘nd well… you know… My name on your lips… geez….” His hands started to rub his thighs. “And…and a few times after that night in Baby too. I tried to stop ‘nd figured you’d never think of me like that again…and then I heard you. You said my name, (Y/N).” He lets out a huge sigh and you could feel the regret coming off of him. “And now… well now… fuck, I can’t even see ya walkin’ around the bunker without gettin’ fuckin’ hard.” He rubs his eyes with the backs of his hands and shakes his head.   
  
You chuckle to yourself when he said he got himself off in the shower since that was practically the dream you just had the night before. Looking over to his lap, you see that he is still half hard, probably from just the idea that now he knows you got yourself off to him too…well at least in your dream. You made a mental note to try and stop talking in your sleep.

“Hey, Dean?” _I can’t believe I’m about to suggest this…fuck it._

He sits back up straight and looks at you. “Hm?”

“I-I could uh… take care of… of that… if-if you want…”

“I-I can’t ask you to do that, (Y/N).”

“You’re not. I’m offering. I’m not you… I don’t go blue ballin’ my friends!” You laughed and nudge his shoulder with yours. “Come on… lay back.” He gives you a small chuckle, reminiscing the moment you yelled at him for ‘blue beaning’ you as you’d called it.  

Soon after, you crawl over to the middle of the bed and wait for Dean to lean back against the headboard once again. He timidly pulls off his shirt and you roll your eyes at him. To help speed things along you hurriedly unbuckle his belt, pop the button and zip down his pants. Your knuckles brush against his hard on and he squirms slightly, taking in a harsh breath. He hooks his fingers into the waistband of his boxers and pushes them down with his jeans, kicking them free. His cock springs free and taps his stomach. You can’t help but lick your lips and crave for the taste of him again. He spreads his legs so that lay between them. You rest your hands on his waist and he threads his hands through your hair.

“You ready?” Your voice comes out raspy from your side smile. He nods and then gentle massages your scalp. You let your lips ghost the tip of his swollen cock and you wrapped your fingers around him. He lets out a blissed moan and then you lick the thick vein from the base to the head. You tease him for a while, caressing his balls while stroking him slowly. Precum leaked out when you dragged your tongue through the slit of his head. His whining groans begged for you to take him in deeper, but he didn’t dare to speak it out loud. You lick kisses all the way up on the right side and then the left. When he is finally slick from your mouth and precum, you take in the head and tease it with your tongue, sucking and pumping him with your hands. Then you adjust your angle so that you can take him in deeper. Inch by inch, he watches as his cock disappears into your mouth.

“Mmm… that feels good.” Dean was taking heavy breaths and his eyes were closed. He tugged at your hair and pushing small thrusts up into your mouth. Picking up your pace, you bob up and down on him faster, hallowing out your cheeks. When you hum around him, he tightens his grip on your hair and pushes your head down further. Large hands move to cup your face and he rubs circles into your cheek with his thumb. You start to move faster and suck harder, chasing his ecstasy. You can tell his is getting close from the fact that his moans are get louder and his grip tightens.

“Ahh… fuck…mmm… yes… (Y/N)… fuck, uuuhg.” And then he pulls you up and your lips leave him with a pop. You look at him confused, wondering why he would stop you. He rubs his fingers across your puffy lips, “I’m close… I jus’ can’t sit here any longer ‘nd not taste you again.” He leans forward to grab you by the arms and pulls you up. He places a kiss on you lips and melts into you. He snakes his arm around you and flips you onto you back. He nips at your jaw line and sucks marks along your neck. He licks at your pulse point and it makes your arch your back. Dean rips the flannel button up in half and tosses it across the room. His fingers hook into your sweats and he yanks them down to your ankles for you to kick them off the side of the bed. He uses his fingers to tickle you sides and then he moves up to squeeze and massage your breasts. Rolling a hard nipple between his fingers and sucking on the other. It was pretty convenient you decided to forego the bra today.

“Ohhh… fuck… this is so much better sober…” You buck your hips up into him, when he flicks a nipple with him tongue, anticipating his hot mouth on your soaking center. He kisses a trail between your breasts and down your stomach and sucks marks on the apex of your thighs. Strong arms push your legs apart. His long tongue swipes up your wet entrance and then he kisses just above your swollen bud. Dean uses his tongue to thrust in and out of you and uses his thumb to rub your clit. He pushes two fingers in and crooks then up to play with your gspot. You squeeze your self around his fingers and your thighs press together trapping his head between your legs. He reaches forward and throws your legs over his shoulders. It seems like he is down there for an hour, edging you to bliss but never allowing you to go over. You had been tugging on his hair and begging him to let you cum, but it seemed having you on the edge was getting him off.   
“Ohh fuck… please. Dean, please let me cum!!” You can feel his smirk against your wet lips. Dean works some kind of magic with his tongue, which you’ll soon come to say is a religious experience and then you are exploding against his face. Rearing your hips uncontrollably, so he holds you down with his rough hands. You bite your lip, almost piercing the skin to hold back from screaming his name. If this was going to work, Sam couldn’t know about it.

“Mmm.” Gulp. “Yes… mmm. Cum for me, baby. That’s it. Give it to me.” Gulp. Your spasms begin to slow down but his tongue doesn’t. Once you gained back control of your breath, he came up and licked your arousal from his lips. He moved up and shoved his fingers in your mouth, causing you to suck off your slick and taste what he made your body create. When he pulled his fingers out of your mouth he kissed you roughly and fought his tongue against yours.

You mumble his name against his lips. “Mm-Dean…?”

“Hmm?” He kept working your mouth on yours and nipping at your lower lip. He let out soft moans into your mouth and pulled out sharp cries.

“Y-you didn’t cum.”

“Mmhm.” He was kissing your neck and squeezing your breast at this point. You were sensitive but ready for more.

You pushed him off of you suddenly and a worried look flew across his face. He didn’t understand why you made him stop kissing you. You caressed his cheek and smiled to reassure him everything was fine… amazing even. “Dean… I-I want you… I want all of you… I want you inside me so bad. Just fuck me… please!”

It sounded like a primal growl. A desperate moan that expressed how much he wanted that as well. He quickly moved to keel above you and then he flipped you onto your stomach. His arm reach around your stomach and lifted you up so that your ass was up and your face was pushed into the pillows. Your hands gripped the sheets and then he used his knee to spread your legs apart. His engorged cock was hot and throbbing against your folds. He slid easily along them making him smooth and ready. Teasing you, he pushed just the head into your entrance, making you buck back into him to try and get him deeper into you. He stretched your walls and you welcomed the fresh sensation. He plunged himself into you in on fell swoop. No easing in or taking it slow. His thrusts were becoming desperate, short and quick. He was chasing his own orgasm but it made you get to your high so quick you felt lightheaded. You ass was slapping against his pelvis and his hand was wrapped in your hair. He pulled hard on your hair, causing your head to lean up far so you could stared at his parted lips. Moving harder and faster, you couldn’t take it anymore. You needed to let go and you wanted see him vulnerable, crushing you with he weight.

“P-ple-ase Dean…I wanna cum… cum with me… cum with me, please!”  
A few erratic heaves and he spills into you. Plowing you into the bed with messy, irregular thrusts. Following after him, he sends you over the edge for the second time, causing a pure white light to swirl your thoughts. His hands fumble with the globes of your ass, digging his nails into your skin. He would leave possessive marks that would last the rest of the week. When your climax began to slow down, he pulls out and turns you back over to your back so you face him. He drops his weight to relax on you and then he ravishes your mouth with his own. He moves to trace soft kisses along your ear and the temple of your head. Then he turned and fell to lay beside you with a huff.

“Wow…” Dean rubbed his eyes with the backs of his hands and couldn’t help but smirk at you.

“You could say that again.” You say that smiling and turning to face him, placing your hand on his chest.

“Wow…”

“We’re…uh… we are in a mess of trouble… aren’t we…” Your lip curls down slightly to frown when you realize there is definitely no going back to the way things were.

“It … hm…only if we let it….”

“Whatta you mean?”

“I mean…. Yer my best bud… and yer in the life… I was born into this crap life…”

You feel a little bit of sorrow; secretly knowing a cookie cutter family is something Dean has always wanted. “Mhm…” You rest your head on his chest, listening to his heartbeat and you trace a scar with your finger.

“I mean…the both of us gotta let off steam once in awhile.”

“Yeah and there’s no fucking way a relationship works with what we do…”

“So maybe…”

“So…maybe we just leave it at this? Best buds… helping each other out every so often? I mean…come on… there is no way we are not doing that again…” you bring in your knees and grab your stomach while you laugh at the complete bliss you had just experienced. “Ha… I thought your reputation was a load of shit… but wow was I wrong.”

He pulls you closer to him so that you are practically lying on top of his chest. “Alright… I’m in if you’re in. No strings attached.”

You gesture a single nod in agreement. “No strings attached.”


	4. Part Four

You were pressed between the back seat of Baby and Dean’s firm body. It had been about two weeks since you and Dean started this little arrangement and you were elated. Consistent sex after hunts without worrying about where the random guy had been or wondering how drunk you were made “reducing stress” all the more easy. Dean parked behind the house where you’d just finished a quick salt and burn hunt. You were both pumped full of adrenaline from digging the grave, when he threw you over his shoulder and tossed you into the back seat. Now the glass of the Impala was fogged and you were seconds from reaching your impending bliss. Sammy left to go talk to the family of the previously haunted house to explain that everything was going to be fine, so you thought you had at least an hour or so before he came back. That is until Sammy’s voice called through the empty street, looking for Dean.

“Shit!” You grabbed your clothes off of the floor and Dean quickly opened the side door, opposite of Sam’s view. He pushed you out and you fell the ground with a thud. He just pulled his boxers to his waist when Sam walked up.

Sam hesitantly knocked on the glass. “Dean… you better have a girl in there.” He opened the door to a half dressed Dean, zipping up his jeans. “Oh… gross! Come on dude! In the frickin’ car? God! At least wait til we get back the bunker! What if (Y/N) came into the car? Uhhg. You’re disgusting.” Dean just smirked and cackled in response. You hating hiding things from Sam but Dean didn’t think he’d understand your agreement, so you decided not to tell him.  

Meanwhile you were listening in while trying to get dressed as quickly as possible.  You smoothed out your hair as best you could and then crawled behind a bush and stood up to walk around the corner. You walked back up to the car behind Sam and pushed your foot back into your shoe.

“Hiya, Sammy!” You were slightly out of breath and patted him on the back, then opened up the door to the back seat.  “Oh whoa! What went on in here?” You laughed and used your sleeve to wipe the fog off the window. Dean climbed back over to the driver’s side and started the engine.

“Oh nothing’… just blowin’ off some steam. Get in Sammy!”

“Uhg…” Sammy used the sleeve of his suit to clean down the seat before he got in next to Dean.

“Stop bein’ a drama queen and get in.” Dean sped off once Sam closed the door. The drive back to the bunker would be about four hours so Dean pulled out the box of cassette tapes and threw on Black Sabbath. Sam, of course was on his laptop already looking for a new case to work on when he turned around to talk to you.

“Hey where did you disappear to after the hunt, (Y/N)? I was hoping you were gunna come with me to talk to the family. You are always good with that.”

“Yea… she sure does play well with others huh?” Dean winked at you through he rear view mirror and you blushed.

Ignoring Dean’s little quip, you focus your attention back to Sam. “I…um I ran off to check back in with the cops. Let ‘em know we got ‘pulled to a new case’. They ate it all up.”

“Hey… uh, (Y/N)… you got something in your hair.” Sam’s eyebrows pinched together and he reached for you. You pulled the twig out of your hair before he reached it and tossed it on the floor. Confused, “why is there a stick in your hair?”

“Hm… musta happened when I was exhumin’ the body.” You thought to yourself that it must have ended up there after Dean pushed you out of the car. “No biggie.”

* * *

You’d finally arrived back at the bunker and you were passed out. Sam still had his head buried in his laptop and he walked straight to his room. Dean carried you back inside, careful not to wake you up. It took all his effort not to tuck you into his bed and fall asleep next to you but he resisted and took you to your room.

“Hey…(Y/N).” He shook your shoulder lightly. “(Y/N)? Wake up… you can’t go to sleep like this. You’re covered in dirt.” You opened your eyes slowly and groaned when you turned over to your side.

“I’m too tired…” Letting out a yawn, your pull your legs into your chest.

“Come on… get up. You’ll sleep better after a shower.” You heard the shower turn on and then footsteps back into your room. The door lock clicked and then arms were lifting you to sit up. His hands griped the hem of your shirt and pulled it over your head.  You let out another sigh and rolled your eyes. Letting your hands replace his, you unhooked your bra and let it drop to the floor. You stood up to walk to the shower and pulled down your pants and underwear. The bathroom was already filled with steam and you pulled back the curtain to climb inside the shower. The water rolled over your skin and you felt more awake. You start to rub the dried dirt off of your skin when Dean climbs in behind you and blocks the stream of water.

“Mind if I help?” He starts to knead the knots out of your shoulders and you stretch out your neck, circling your head around a few times. His hands leave your shoulders and the water hits your back again, soaking your hair. Dean squeezes a dollop of shampoo into his hand and then begins to lather it into your hair. Long fingers are massaging your scalp and you feel kisses on the side of your neck. “Wanna finish what we were doin’ when we were so rudely interrupted?”

He spun around so that the water could wash away the suds. His hands brushed through your locks and he pressed a kiss on the tip of your nose. You thought to yourself how it was funny that your small hands barely covered even half of his bicep. You finger lingered over his left shoulder and you noticed the almost completely faded scar of Cas’ handprint.

“So remind me again, (Y/N)… what were you sayin’ earlier today in Baby?“ You were washing Dean’s hair while he soaped you down with the loofa. “Somethin’ along the lines of ‘you need me’?” You rolled your eyes at him and turn around to face away from him and let the water hit your face. “And I bet if Sammy hadn’t walked up, I coulda made you plead all over again.” All of the soap and shampoo had since flowed down the drain and the warm water was starting to run cold.

“Prove it, Winchester.” Dean’s toned arm wrapped around your waist while the other secured under your ass. You wrapped your arms around his neck as he pulled back the curtain and stepped out back into your room. Water dripped off of your bodies and left puddles on the floor. You could feel his throbbing cock pressed against your stomach and it brushed softy against your clit when he walked over to the desk. He kicked away the chair and pushed off the papers that covered the top. You were sucking a mark on his neck when he sat you down and spread your legs. He grabbed his shaft and rubbed the tip up and down, through your soaked entrance. Your hands greedily grab his ass to try and pull him forward but he pushes himself away.

“Ha. Eager much? Seems like you’re awake now, huh?”

“Shut up and fuck me. It’s been a long day.” He attacked your mouth, devouring your cries. He pushed into you excruciatingly slow and chuckled when you thrust your hips forward. While clenching his shoulders for support, your nails dug into his skin and he gripped your hips. He hammered quickly into your core, chasing his itch. The drawers of the desk were opening slightly and slamming shut from the shaking of the desk. It wasn’t long after that you felt that familiar tightening in your core. No man had ever gotten you to cum as quickly as Dean had and he even gave you a new record for number of orgasms in an hour. It was the best sex you had ever had. It was a raw, eager and a voracious form of sex. After this arrangement has started, hunts had gotten solved quicker, Dean and Sam didn’t bicker as much and you were all together in a better mood.

Dean had folded you body practically in half and he was laying over you, holding your ankles. This was one of his favorite positions because he could get remarkably deep inside of you. “Ohh. F-fuck… (Y/N). I’m close…” His thrust slowed down and changed angles. Each drive hit your gspot and you gasp every time his pelvis met yours. Your walls fluttered around him and then burst into full-blown trembling. “Shit… you’re so tight around me… oh-my…” He exploded with a loud moan and streams of his cum coated your walls. He filled you up and you fucked him back harder and faster, send you over the edge again. After catching his breath, he pulled out and walked backwards to collapse on the bed. “Shit. You really are the best friend a guy could ask for…”

* * *

The next morning the boys were in the kitchen eating breakfast. You were in your room on the phone with Charlie who called to ask help for case she was trying to solve. “No… Charlie, I think you’re dealing with a werewolf. It’s textbook. The boys and I ganked one not too long ago. Why don’t you come by the bunker and we’ll help you out, okay?”

“Yeah… I guess. But only if you tell me more details about this secret fuck buddy you’ve got going.”

You giggled at her persistence, “it’s no big deal, Charlie. It’s just some guy in town that likes to meet up. Sure… he might be the best sex I’ve ever had but I’m not about to let myself get attached. You know that could never work with what we do…”

“Okay… well at least tell me the details. Just because it’s not the same team that I play on, doesn’t mean don’t I enjoy a story or two. Oh my God! Is he big? Like big—big?” You could hear her smile over the phone. You imagined Charlie making size gestures with her hands as if you could see her.

“Let’s just say that there are no complaints in that department.”

“Wow. But hey… I always say it’s the not the size of the wave but it’s the motion of the ocean that counts.”

Charlie never failed to make you laugh. It was going to be nice having another girl around the bunker. It wasn’t that you were getting tired of the boys, but to talk about something other than shaving technique and new workouts was going to be a good change of pace. “Alright. I’ll see you in a couple hours, Charlie. The boys are going to be happy to see you.”

“Peace out, girl.”

* * *

You thought it would be a nice surprise for the guys if you didn’t tell them that Charlie was coming for a visit. It had been a great couple of weeks with a lot of wins on the hunting aspect of things. So a night of drinking and games to celebrate with Charlie would be fun. There were a few knocks at the door so you ran up the stairs to let her inside.

“What’s up, bitches!”

“Hey, Charlie! What are you doin’ here?” Dean was beaming with excitement. Charlie was like the little sister he never wanted but got stuck with anyways. But he loved her completely. “Did we miss your call or somethin’?”

“(Y/N) didn’t tell you? She told me to come by and you’d all help me with this werewolf hunt.” She planted a tight hug around Dean and then onto Sam. You ran into the kitchen to grab a bottle of whiskey and then rushed back into the library.

“Wolf hunt… sh-molfunt… we are drinking tonight!” You punched her on the shoulder and she attacked you with a bear hug. Pouring four glasses of the amber liquid, you smile over at Dean while he is huddled over, grabbing his stomach, nearly falling to the floor while Charlie jabbers away.

Sam walks up to you and nudges your shoulder. He picks up two glasses and nods over toward the two laughing hooligans. “It’s nice to see Dean laugh like that again. He’s been in such a great mood lately… considering…”

“Considering what?” You took a quick swig out of the bottle and then topped of each glass with another splash.

“Well, considering he hasn’t gotten laid in a really long time… I mean not that I know of. He hasn’t taken a girl back to a hotel in weeks.” Sam downed the liquor in his glass and then filled it back up.

“Maybe he realized how an endless line of one night stands wasn’t his thing anymore…” You eyes travel up and to the left from the lie. You sipped on the whiskey silently wishing Sam would change the subject.

He looked at you like you were insane. “(Y/N)… this is Dean we’re talking about! Dean… remember? There is no way he could hold out for this long.” He rubbed the back of his neck, “he’s hiding something. I can tell.”

The only way out of this conversation was for you pick up the glasses and walk towards to others. Charlie was in the middle of whispering something into Dean’s ear when you handed her a glass. Sam was a step behind you and passed one to his older brother. Charlie pulled away from him slowly and Dean’s eyes were burning into yours. The smirk on his face was immaculate. He took a large gulp of his drink and them smacked his lips.

“So (Y/N)… Charlie here tells me you’ve got some kinda secret fuck buddy.” He takes another mouthful and then leans back in his chair.

Sam jumps and nearly falls out of his seat. He spit out what was in his mouth from surprise, “What?!” He looks at you wide eyed and startled by the guilty look on your face. “Hello? Earth to (Y/N)? You still in there?”

“I-I um…” You cheeks were beet red, partially from the whiskey and partially from the fact that you normally never talked to the guys about your sex life.

“Apparently you told Charlie it has been ‘the best sex you’ve ever had’.”  Another smirk wiped across his face and he finished what was left in the glass.

“So do we get to meet this guy? Is he a hunter?” Sam leaned in closer to you. He looked like a child during story time. He chin rested on fisted hands and his big curious eyes were waiting for you to answer.

“No… he’s a … um… It’s none of your business guys!” You stood up to go grab the half empty bottle and filled up your glass again. “So uh… tell us more about this case, Charlie!”

“Sorry babe, you aren’t getting off that easy! You promised you would tell me all the details!” She grabbed the bottle from you, topped off her glass and then Dean’s that was sitting on the table.

“Yeah, I’ll tell you! Not these nosey buttheads.”

“What’s the difference? Dean’s your best friend, isn’t he? You should be able to tell him this kind of stuff, right?” She made a gesture with her hands to the boys trying to guess at how big the guy’s dick might be. Sam laughed so hard some of his drink spilled onto his shirt.

“Yea… I’d say you’re right, kid.” Dean sat up straight and tapped his glass against Sam’s in cheers. “I wanna know more about this guy. Like where the hell did ya meet him? And how the hell do you have time to get away from us to go meet up with him?” Dean was smiling against his glass while the whiskey hit his lips. You were giving him a not so subtle death glare when Sam came to the rescue.

“Okay. Okay, guys. Enough. She clearly doesn’t want to talk about it, so let’s drop it.”

“Whatever.” Charlie giggled and rolled her eyes. “But once these guys go to bed, I’m going to try and get more information out of you again.”

You let out a relieved sigh and finished up your drink. You made a mental note to yell at Dean for making you feel so uncomfortable once you had a moment alone. Then you thought to yourself of a few other punishments your rather dole out that would make him suffer. For the rest of the night you watched Charlie and Dean argue over ‘who shot first’ in Star Wars and then she tried to explain the plotline of Harry Potter to Sam. It was a good night filled with friends, liquor and laughs. But after everyone passed out, you spent the rest of it in bed internally plotting your revenge on Dean.  He was in over his head for teasing you the way he did in front of them and you wanted to remind him that he didn’t hold any power over you.


	5. Part Five

Charlie ended up staying around for a few days. It was crowded and there were too many pairs of ears in the bunker especially when Castiel would come to visit. So you told Dean you’d thought it’d be best not to fool around in the bunker for a few days. Sneaking around was fun but you didn’t want to risk the whole pact going to shit if someone caught you. That meant no sex for you or Dean for the week. As much of a struggle it was for you not to get laid, it was entertaining to watch a sexually frustrated Dean try and solve a case. Dean could have easily picked up any girl from the bar or taken you to a motel but Sam had kept all of you busy with back-to-back hunts.

After Charlie left, Sam had found a case in Iowa where a family had a vengeful ghost living in their attic. One quick salt and burn later and the woman was asking to take the three of you out to dinner with her wife as a thank you. It was completely out of character to accept this kind of gesture but it had been a million years since you had been to a fancy restaurant and you could tell Sam and Dean were drooling at the mouth from thought of prime rib and lobster.

So here you were, sitting at a cloth covered table, making chitchat and sipping on a $250 dollar glass of champagne. Dean was keeping his head down avoiding the conversation while he chewed on his prime rib. Sam was pleased to be socializing with other people than the two of you. Conversation topics were limited to food, hunting and old movie references in the bunker, so for Sam to be given the chance to release his inner Stanford was a nice change of pace. You made the boys wear their cleanest suits and you wore the best dress in your closet. Dean was sitting to your right and Sam, across from you. Sam was in the middle of talking to the couple about a plea bargain that was announced on the news last night while Dean was taking a sip of his beer when your hand rested on his thigh, giving it a small squeeze. Your hand slowly moved down into his inner thigh and he jumped an inch off his seat and almost spilled his drink.

“Whoa everything okay there, doll?” The woman gave a worried look to Dean. You tried to look as innocent as possible when Sam began to question him as well.  

Dean coughed into his elbow and shifted in his seat. “Huh? Oh! Yeah. All good.” Your hand was moving higher, inch-by-inch. He was already hard when you got to his tented pants and his thighs pressed together when you began to palm over his erection. You were trying to be as discrete as possible but at this point of the night you had four glasses of champagne. You generally had a high tolerance for alcohol but for some God forsaken reason, champagne makes you want to take all of your clothes off and go skinny-dipping. Dean was loosing his concentration on eating his food. Every few bites he had to pause and suck air through his teeth.

“Wow, Dean. You are really enjoying that prime rib…” Sam’s eyes were wide and amused. “How about we splurge and get an extra room at a hotel tonight for you and that piece of meat?” He chuckled at his own joke and returned his attention back to his conversation when Dean rolled his eyes.

You grabbed Dean’s hand under the table and linked your fingers into his. Letting your entwined hands grab the edge of your dress to pull it up. His hands gained control to advance toward your heated center. To his surprise you weren’t wearing any underwear. You let him barely graze your folds when you pushed his hand away and stood up.

“Excuse me, please. I need to use the restroom.” Sam smiles in return and sarcastically thanks you for the play-by-play. You give Dean a subtle wink and leave then table. The restrooms were fancy and each has its own waiting section with cushioned chairs and tables.  You were thankful to find that the door had a sturdy lock. A few minutes after you’d left, Dean was knocking on the door. The second he was able to close and lock it behind him, he had you pushed up against the door nibbling at your upper lip. He scrunched up your dress to pool around your waist, letting his long fingers slip through your wet folds.

“God, I’ve been waitin’ all week to do that. I can’t believe I was able to hold out as long as I did…” He presses himself against you and his cock bumps into your thigh. When his hands thread through your hair, he attempts to lean in for another deep kiss but you push him away. His faced is covered in confusion and he leans in again. You push him away for the second time and click your tongue alongside your cheek.

“So…we never got a chance to talk about that first night Charlie was here this week.” You start to undo his tie and unbutton his shirt.

“Ahh…you still sore about that, bubs?” He pulls off his belt and unbuttons his pants and they fall to the ground leaving him in only his boxers. “I was only teasin’ ya. But I gotta admit it was pretty funny to see you all flustered.” You grab him by the neck and pull him in for a rough kiss. Switching places with him, he is pushed against the door, letting his hands roam your body. He pulled your dress over your head, unclasped your bra, letting it drop and cupped your breasts in his hands. Massaging them and pulling at your nipples, making them hard and sensitive. You push yourself away from him again and pick up his belt off of the floor. You notice a chair sitting in corner of the fancy bathroom and drag it to the middle of the room.

“Sit.” Dean was taken aback by your sudden dominance. In sex, he was all about pleasuring the other person by controlling. This was the first time you’d expressed dominating him completely. He cowered over to the chair and tried to get comfortable. “Hands behind your back.” You fastened his leather belt around his wrists and secured it to the back of the chair. The silk tie covered his eyes and tied around his head. You pulled out a scarf you had in your purse and lightly gagged him. Dean could hear the click of your heels as you circled around him.

“You really put me on the spot in front of Sam and Charlie…” You dragged a single finger across his back and shoulders causing goosebumps to rise. Then you straddled his lap and ran you hands over his chest. You start to grind your hips over his tented arousal and he lets out a muffled moan. “I was a little humiliated to be honest. I think you deserve to be punished.” Trying to gain some control, he bucks his hips into you. You swing your leg off of him and kneel on your dress in front of him. He lifts his hips up slightly allowing you to pull off his boxers. Your fingers draped his engorged cock and began stroking. Precum is already leaking out and the head was throbbing.

He spits out the gag so he can talk. “Ohhh… fuck. That feels good. I want your lips on me…” You chuckled and press a light kiss on the tip. Your head lowers and your mouth devours his shaft. While massaging his balls you hum around him, causing him to throw his head back and groan loudly. You bobbed your head up and down quickly and sucked hard around him, using your hands to stroke the difference. “Mmm… I’m close.” Suddenly, you pulled up with a pop and he threw is head back up from shock. “Wha-why did you stop?” You didn’t answer him. You just stood up and walked behind him. “(Y/N)?” Next, you are careful not to make a sound. You glide your tongue on the edge of his ear and nibble the lobe. You let your hands snake over his shoulders and squeeze his nipples. “Shit….” Pulling away again your quietly grab you dress, slipping it on without a sound. Threading your fingers through his hair, you roughly pull his head to the side. Sucking and biting marks on his neck, you lick his pulse point and it makes his cock jump. Freeing him again from your grip, you step back and lean against the door, taking a moment to admire your friend in this vulnerable state. “(Y/N)?”

 _Okay. Here is goes. All or nothing. This’ll get him back for what he did!_ You pick up his clothes off the floor, leaving just his boxers and stuff them into your purse. You quickly brush your fingers through your hair and smooth out your dress before kissing Dean on the tip of his nose. Without another word, you unlock the door and leave.

“Hey everyone! Sorry about that. Long line for the ladies room.”

Everyone had already ordered dessert and was half done. Sam looked up from his bowl of fresh fruit, “that’s okay. I ordered you chocolate cake and Dean some cherry pie. Have you seen him by the way?”

“Wasn’t he was still sitting at the table when I left? But I think I saw him talking to some waitress over there by the restrooms.”

“Yeah and he’s been gone for long time.” Sam scanned the restaurant looking for his older brother.  

No matter how hard you tried, you couldn’t help but smirk while eating your cake. Dean was probably pissed off. You knew that flimsy faux leather belt wouldn’t hold him in the chair long. But it was amusing to think of him trying to figure out how to escape the restaurant in his boxers without being seen.

“So Ana, tell me. How long have you and Jennifer been married?” You needed to make the small talk seem normal to avoid Sam from getting more curious about Dean’s disappearance than he already was at the moment.

“Just over three years now. I just got telling Sam here that we are currently going through an agency to adopt!”

A moment later the restaurant fills with gasps and then becomes dead silent. Dean wearing only his boxers comes stumbling out of the hallway. All eyes are on him and he is beet red in the face. Sam spits out the wine in his mouth and nearly falls out of his chair. Dean had his hands covering his area while he sidestepped his way out of the restaurant.

“Oh my God. I-uh… I think we better go. I’m sorry about all this.” He looked to Ana and Jenny who both looked like they were on the verge of bursting out into laughter. They didn’t know the three of you very well, so you assumed they must have been holding back. So to break the tension, you let yourself fall into laughter and watched them join you in the hilarity.

“Does this happen often?” Jenny took a few more bites of her dessert and looked intrigued.

Realizing that the keys to Baby were in Dean’s pocket, which was currently in your purse, your eyes widen at the thought of Dean hiding behind the Impala waiting for you to come outside. “Oh, on the daily, but I think Sam’s right. We’d better go.” Digging around in your bag, you pull out the keys. “I’ve just realized I have the keys to the car. Dean is probably freezing.”

“Serves him right for whatever he did to that poor waitress!” Sam seemed mildly annoyed but mostly amused. “Alright, let’s go. Thank again for an amazing meal. I can’t remember the last time I had wine that didn’t come out of a box.”

You parted ways with the lovely couple and headed for the car. Dean was sitting along the curb next to Baby with a pouted face. When the two of you walked up to him, Sam passed him is coat but Dean’s eyes were fixated on you. Then he grabbed it and slipped it on with an annoyed grumble.

“What the hell man… You couldn’t wait until after dinner? Just let me know next time you decide to show a waitress a good time and we can get a motel. Okay? Enough of the public restroom and car sex!” Sammy was only being half serious. He was just as guilty as his older brother for letting that part of himself take over. “What the hell did you do to make the girl grab your clothes and dash anyway?”  

“Apparently, I’m a loud mouth.” His eyes hadn’t left yours and you shifted your shoulders from the shiver that ran down your spine. So you tossed him the keys and he opened the trunk to grab some extra clothes he kept for emergencies. After he got dressed, he climbed into the front seat and started the engine. You didn’t dare to slide in next to him. Instead you let Sam take shotgun and you got into the back seat. The whole car ride back to the bunker was just Sam trying to break the awkward silence with useless random facts. Dean didn’t say a word even when you tried to play along with Sam. When you finally did arrive home, Sam jumped out of the car and practically ran inside.

“Dean, you comin’?”

“Yeah. I’ll catch up in a sec, Sammy. I need to have a little chat with (Y/N) first.” Sam closes the door behind him and you are left alone with Dean in foggy silence. The tension was thick but you couldn’t decipher if it was sexual or anger. You were leaned up against the hood of Baby and Dean paced back and forth in front of you with his arms crossed. You were trying to stay serious because it was obvious he was ticked off but images of Dean ducking through the fancy restaurant in only his boxers was clouding your focus. So you try and hold back a chuckle but it’s obvious since you cover your face and let out light giggles.

“Alright. You had your fun.“

"I’m really sorry that I’m not sorry.” You allow your laughter to take over.

“Just my boxers? Really? It wasn’t funny.” You could tell behind the embarrassment, Dean was laughing. He knows this would be the kind of joke he’d play on you or Sam if he had the chance.  

“Oh lighten up! I was just getting you back for making me feel uncomfortable around Sam and Charlie! You’re just sore because I tied you up and you like to be in control…”

“That is beside the point… I thought you didn’t blue ball your friends! Your words not mine. And you left me high in the sky blue…”

“Yeah… my bad bud. I’ll make it up to you. Promise. But it was fun seeing you tied up like that. I’m generally the more submissi-” Dean cut your sentence short when he pushed his lips onto yours. The kiss was deep and rough and it caused you to sit back on the hood of the car. Dean lifted you up slightly so that you could lay back. His body covered yours completely. The radiating heat from the engine was still lingering on the hood but a chill still ran through your entire body. His hands were flat on the car, each near the sides of your head. He lifted up and stared at your startled expression.

“You’re right. I do like control. And you need to be reminded of that.” Dean’s hands rip you dress in half. The cool breeze from being outside made you shiver. He warmed you up with kisses down the valley of your breasts and over your stomach. His scruff tickled but it made you buck your hips up into him inducing a primal groan from Dean. His hands gripped your thighs and spread them apart so that his face was buried in you’re warm center. His tongue was rough and impatient like he was trying to break a new record. When you tried to sit up and lean on your elbows, he pushed you back down and held you in place. Within seconds you were cumming hard on his face and he was fucking you with his fingers. After he pulled his fingers out he shoved them into your mouth, making you suck on them. Once he was satisfied that you cleaned him up, he flipped you over so you were chest flat against the hood. You could hear the ruffling of his pants falling off and then he slams into you. He bottomed out in one fell swoop and the sudden stretch of your walls made you scream. There wasn’t anything for you to grip onto while is pummeled into your core. He wrapped your hair around his hand and with the other, he slapped your ass. The thrusts were fast and irregular. You started to cry his name so his hand covered your mouth to keep you quiet. You finally bit your lip to hold in your whimpers and Dean moved his hands to your hips so that he could pull you onto him hard. You came for a second time around him and you felt like you were going to blackout. He pulled out, threw you up over his shoulder and tossed you into the back seat.

“Now ride me like a good girl.” Dean sat comfortably on the leather seat and you straddled his lap. You grabbed his erect cock and guided him into your entrance. He unclasped your bra and tossed it onto the floor. Taking his time, he gave each breast its own attention, carefully sucking on the nipple and massaging the rest. You began grinding your hips against him, interchanging the rhythm and pace. You bounced up and down on him and your walls clenched around his shaft. You felt close to your orgasm but then he grabbed your hips and stilled inside of you. Dean rolled you over to lie down on the seat so he was on top of you.

The entire mood of his intentions flipped like a switch. His thrusts were slow but firm. He nuzzled his face into your neck kissing sweetly and lovingly. His hands roamed your body adoringly rather than with his usual domineering intents. Then he simply just stared into your eyes when your thrusts matched his in the middle. He kissed your lips gently and affectionately and his thumb caressed your cheek. His sudden devotion scared you. It was always just sex up until now and it felt like you were making love.

“I’m close. Cum with me, (Y/N). Please…. Cum with me.” Dean pressed his forehead to yours and a few thrusts later his was letting go. He came hard with passion and concentrated tenderness. Your name was the only thing he could muster out followed by intense moans. You came for the third time just after him, moaning frenziedly and gripping your hands in his hair. Your walls pulsated slow and hard. It was the most intense orgasm you’d ever experienced. It seemed like you were both cumming forever but when he finally stilled in you again, he didn’t pull out. He pulled you in tighter and kissed you gently. With no hesitation, you kissed him back. Then he laid light kisses all over your face. He placed them on your cheeks, the corner of your eyes and on the bridge of your nose.

It was quiet and the only sounds were labored breathing and an owl hooting outside. You felt the need to say something but you couldn’t put together words. “I-I… um… that was, uh…” _Shit I don’t know what to say. That was really intense._ He was still on top of you and he rested his head on your chest.

“Yeah…” You could have sworn he looked guilty. _Does he think he took this one too far? What is he thinking? He is being was too quiet._ One of the rules made for this arrangement was that if either of you began to have feelings for the other, you would end it. You just never thought Dean would be the one to make that misstep.

“Are you alright?” You began to stroke his hair. He didn’t answer you back, only letting out a drawn out sigh. After a few minutes he stood up and got dressed. He got out of the car and walked inside the bunker without another word. You sat in shock for a few more minutes before going outside and picking up your dress to slip it back on.

No matter how hard you tried, you couldn’t fall asleep that night. The thought of Dean’s green eyes staring into your soul kept you awake. You didn’t want this to end but most of all you didn’t want to lose your best friend. All you wanted to know was what he was thinking. Was this his way of telling you that he thought of you as more than a friend? Or was this one last hurrah before he nipped it in the butt? Only tomorrow would be able to tell you what would happen. At least Castiel said he was going to spend the day with you guys tomorrow. Some distraction from these unclear reflections could help. You’d rather let all of this marinade for a while before having to deal with it.


	6. Part Six

**Notes for the Chapter:**

> Part 7 will be the last installment of this series! Thanks for reading!

Dean ignored you for most of the next day. He wouldn’t look you in the eye and didn’t even eat the breakfast you made for everyone. He’d leave every time you walked into a room and locked his door, which he usually kept open. You were wracking your brain, trying to figure out what was wrong. To you, the sex last night was intense and mind-blowing. Maybe you had been reading the signs wrong. Was it possible he wasn’t into this deal anymore? Did you say something out loud that was meant to be just a thought? Did he think you were in love with him after last night? You didn’t even know what you were feeling. The only thing that mattered to you was keeping your best friend in your life.

Castiel asked to hang around for a couple days and you were glad to have a friend to keep you distracted from the constant pestering your brain had in for you. Although Castiel often had his head in the clouds, he was also observant to details. He noticed you weren’t acting yourself and when you brushed him off when asked about it he didn’t pressure you to divulge in it any further. A few gusts of wind later and Cas was standing in front of you with a game board in hand.

“How can this human shaped plastic go to college and get a career?” He had a little pink plastic figure rolling between his fingers. His eyes squinted to get a better view and his head tilted from the curiosity.

“They represent people, Cas. And college and having a career are what normal people call a milestone in life.” Your voice sounds lightly disheartening. It was the life you would never be able to live since you were a hunter. There was only one way you’d be leaving this world and it would be guns blazing. You accepted that.

“Sammy?” Dean walked into the library looking for his little brother. He didn’t know Castiel had already arrived and was startled to see the two of you together. “Oh hey, Cas. Whatta doin’ here?” Again ignoring your presence.

“I am here to assist as needed in cases for a few days. And I felt (Y/N) calling out to me this morning. She isn’t feeling too well.”

“Oh. Uh…yeah. Okay.” He awkwardly walked backwards out of the room. “If you see Sammy, let him know it’s his turn to clean out Baby.” You roll your eyes at him but he doesn’t notice.

“Okay. Your turn, Cas.”

 _Is everything all right, (Y/N)?_ He was talking to you through thoughts. _It seemed as though I came upon an awkward situation._ He spun the number wheel and moved his piece. _Are you and Dean no longer friendly?_

“What?” First thought that crossed your mind was that he knew. _Oh God he knows._

 _Knows what?_ He looked up at you with squinted eyes.

_Shit. That’s right. He can he my thoughts._

“Yes, (Y/N). I can hear your thoughts. But if there is anything you don’t want me to see, just imagine a door closing… As I was saying, are you and Dean no long having sexual relations?”

Practically chocking on your own saliva, you are caught off guard and coughing uncontrollably. “Wh-what? Cas? How did you know that?”

“I-uh. I heard you screaming one night and I thought you were in danger. So I flew in and saw you and Dean in uh…compromising positions. Common ones that humans use when producing children. I left quickly before either of you noticed. You seemed to be in safe hands.”

Your cheeks were bright red. “Crap. Cas, you can’t tell anyone about this.”

“Why? I thought people in love liked to express that with other people they cared about.”

“We aren’t in love, Cas…. We are just having- were having sex.”

“But sex is an expression of love, is it not?”

You let out a disheartening sigh. “Not always…Dean and I were just… helping each other out… as friends. You know? Besides. It’s over now. And I’m pretty sure Dean hates me.”

“He doesn’t hate you.” He paused midturn and placed a hand on your shoulder.

Looking down at your lap, “Cas, he’s been avoiding me. Something weird happened last night and now he won’t even look me in the eye.” You let out a hopeless sigh and Cas pushes the turn wheel to you. Before you pick up a career card from the pile, Sam walks into the room.

“Hey guys!” He was panting and sweating. You assumed he must have just gotten back from a run. “What are you guys playing?” Castiel hold ups the cover, reads it out loud and then takes his turn. “You okay, (Y/N)? You only like to play board games when something is bothering you.”

You let out a melancholy sigh. “Yeah… Sure. I’m fine, Sam.”

Cas tilts his head to Sam, “She’s not fine. Dean, he-” but you cut him off with a kick to the shin before he could finish his sentence. “Oh I um… I still don’t understand how one of us can win at the game of life.” He picks up a house card and shakes his head. “Sam, Dean was looking for you earlier. He says that it is your turn to clean out the car.”

Slightly confused about what just happened, he just brushed it off his shoulder. Suddenly realizing what Cas just said, “what?! I just cleaned it out last week!”

You chuckle at his whining. “Guess it’s your week again, buddy. Better get goin’ before Dean gets back.” You give him a small smile knowing it probably should be your week but you were too distracted to focus on something as detailed as cleaning out the Impala. Frankly, you didn’t want to spend any more time with something that reminded you of Dean.

After Sam left for the garage, Castiel asked you if you’d accompany him to the park. Feeding the ducks made him happy and he figured some fresh air would do you some good.

“Okay, Cas. But let’s go to the feed store first.”

* * *

Back at the garage, Sam had already filled a garbage bag worth of empty salt containers and fuel cans. He was digging in the back seat when he saw some black fabric underneath. He had to lie down on the floor and extend his long arm to reach it. He pulled out a laced black bra and examined it for a few seconds.

Talking to himself, “what the hell is this doing here? Dean hasn’t hooked up with a girl in weeks…” He set it aside and decided to ask Dean about it later. He figured it was probably just from a hook up a while back and they missed it on the last clean up.

Bra in hand, Sam walked in the library to find Dean skimming through a magazine and eating a burger. He quietly sat across the table from him and Dean didn’t so much as glance up from the page he was reading. So Sam tossed the bra on top of the magazine and Dean brought up his attention.

“Aw Sammy, you shouldn’t have! But I think you got the wrong size. You look more like an B cup to me, little brother.”

Unamused, “I found that in the car. Something you wanna tell me?”

“What? You want me to give her your number? Didn’t think you were one for sloppy seconds.”

“Uhg geez, Dean. No! But I know you haven’t hooked up with anyone in weeks, so care to explain where this came from?”

Dean awkwardly shifted in his seat. “Relax man. I hooked up with that waitress from last night. After you went inside, (Y/N) followed in after you ‘nd I drove back.”

“That poor girl actually gave you another chance?”

“I just flashed her some of that sweet blue steel ‘nd she couldn’t resist.” Dean gave his brother his Zoolander inspired smug look and blew a few air kisses his way.

Sam rolled his eyes and grumbled annoyingly. “Okay, okay. I get it. Just next time clean up your mess.” Dean just gave him another smirk and chuckled under his breath. He picked up his empty dish and left to take it to the kitchen. Sam picked up the black-laced bra and hung it up on one of the bookshelves. He figured it would be a funny reminder for seeing Dean walk out naked at the restaurant. Dean locked himself in his room again doing only God knows what and Sam pulled out his laptop to search for a new case. A few gusts of wind later and the flutter of wings filled the room.

“No, I’m telling you Cas, bread crumbs are unhealthy for ducks! It makes them sick!”

“Then why are there always people throwing it into the water?” He tossed a half empty bag of duck pellets that you made him buy onto the table.

“Because they don’t know any better but now you do. Heya Sam, what’s up?”

“Just trying to find us a case to keep us busy until we hear back from Bobby. Where did you guys go?”

“(Y/N) and I went to the pond to feed some ducks.” Castiel was currently pulling and tugging at the black bra hanging on the bookshelf. “Why is there a woman’s undergarments displayed on a bookshelf?” He was pulling at the straps and he accidently flung it across the table, landing in front of you.

“Hey! Where did you find this? I’ve been looking for this all day! It’s my favorite bra!”

“Oh I found it…uh…” Sam’s eyes widened and he quickly looked down at his lap. “Um… wait. No, I uh what?… yeah. Um yeah. I found it in the uh… laundry room. Yeah…” His eyes shifted to Cas, who was busy playing with a duck feather he found in his coat pocket.

“Why are you being so weird?” You picked up the bra and headed for your room. “Come on, Cas. Let’s go binge watch some Netflix.” Castiel gave Sam a quick wink when he passed him, following you into the hallway.

“You sure you’re okay, (Y/N)? You’re the one who has been actin’ weird all day.” You were too far gone into the hallway to hear him. Sam was left to himself in the library dumbfounded by what just happened.

* * *

“What the hell do you mean it’s been goin’ on for months?”

“Meanin’ it’s really none of your damn business, Sammy!”

“I can’t believe you would be so stupid and do this to (Y/N)!  You might be emotionally inept to this sorta thing but she’s not! You broke her heart, didn’t you? That’s why she’s been acting all weird lately. You just hit it and as soon as there was a smidgen of emotional intimacy, you bailed, didn’t you? She started to fall for you and you couldn’t handle it.  God, Dean. You’re only thinking about yourself!” Sam was losing his breath from yelling loudly.

Dean spat back, “you don’t fuckin’ know what your talking about, so shut up! This is between me and (Y/N). That’s it.”

“It’s not that simple, Dean. She lives with us. She hunts with us. What he hell did you guys expect? That being friends with benefits was going to last forever? That no one else around here was going to notice?”

“It doesn’t matter now. It’s over.” Dean slammed the laptop shut and started fiddling with random items on his desk.”Besides we were good at hiding it. You almost caught us a bunch of times and were still clueless.” 

“Oh my God. That time in the car after that ghost hunt last month?” Sam had a small face of disgust.

Dean lets out a chuckle, “yeah.”

“Uhg and that time I yelled at you to turn the volume down? Geez I thought you were watchin’ porn…” He closed his eyes to try and avoid the memory of the moans and cries that rang through the bunker.

“Yeah then too…” He frowned slightly and sighed.

“Holy shit! And last night?” Sam’s hands flew to his head from the realization.

“My clothes are still in her purse. She was gettin’ back at me for teasin’ her when Charlie was here.”

“Oh my God…”

“Yeah, you really are pretty clueless, lil bro.”

“Well no matter what happened… Dean, you’ve gotta fix this. You can’t just ignore all of it. Talk to her. Let her down easy and maybe she’ll get over it and things can go back to the way they were.”

Dean was twirling one of your hair ties in his hand. He jumped to fall on his bed and buried his face into his pillow. The smell of your shampoo still lingered on it and it made him breathe deeply and close his eyes. “Th-that’s not why… why I…”

“No way…”

“Shut up.”

“You love her don’t you…?” Sam sat down at the edge of the bed, facing away from the elder Winchester. "You do… Don’t you, Dean.”

“It was me, Sammy. I was the one that took things too far. I screw this up. We had a real good thing goin’ and of course anythin’ good going on in my life, I destroy it.”

“That’s not true…”

“It is… ‘nd now the best thing to ever happen to me is gone because I fucked it up.”

“She’s not gone, Dean. She’s right outside, in her room watching tv with Cas. You can still fix this.”

“There’s nothin’ to fix, Sam. I am who I am and I’m a fucking beacon for hurt and destruction. If any word got out that… ‘nd if she got hurt? I’d never… I couldn’t forgive myself.”

“That’s why you’re ending this!? Because you’re worried about her safety?! Let me ask you, how long has (Y/N) been hunting with us now? How many times has she actually saved our asses? (Y/N) is strong and she can hold her own. And by now the whole fuckin’ supernatural world knows that she is important to us. So stop making bullshit excuses to avoid happiness for yourself, Dean. You deserve to be happy for once.” Sam gets up and storms out of the room, slamming the door behind him.

Meanwhile in your room, you were in the middle of watching an episode of Gilmore Girls with Castiel. You could hear muffled yelling through the walls but the words were indistinguishable.  

Referring to the two girls on screen, “why are they talking so fast? Are they in a hurry?” Castiel pulled the blanket tighter to himself and reached for some popcorn.

“I think it’s from all the caffeine to be honest.” You are distracted again from the yelling, looking toward your bedroom door. “They are being really loud. I haven’t heard them fight like that in a long time. Should I do something?” Then you hear the slam of a door and silence.

“No, I believe they are done now.” Cas pushed the bowl onto your lap and looked concerned when he noticed you weren’t watching the show. He tried to encourage your attention back to the tv to avoid any more anxiety over the situation. “(Y/N)… why did this Lorelai name her daughter after herself? I thought that’s was only traditional in the male sense.”

You give in and turn your focus back to Cas and Netflix. “She’s a progressive feminist and I find it refreshing.” There is a soft knock at the door and then it creaks open. Dean is rubbing the back of his neck with his hand and he stumbles over his thoughts.

“Hey, uh Cas… can you give (Y/N) a moment alone?”

“Of course, Dean.” _Poof_. He was gone with a small draft and the tv clicked off.

 _Oh geez, this is it… he is going to end it. Fuck. I knew I screwed everything up last night. Fuck. I’ll just tell him I slipped up and it didn’t mean anything. No strings attached. That’s what we agreed on._ You scoot over the bed slightly so that Dean could sit down. “Hi.”

“(Y/N)… we need to talk…”


	7. Part Seven

**Notes for the Chapter:**

> This is the final part of Best Buds! I had a blast writing my first ever mutli part fic! Thank you for sticking around and reading until the end! 
> 
> Note: Flashbacks are in italics

_“Ohh my God! Yes! Dean!! Fuck… please! Shit… fuck me harder!” Dean was pummeling you into the mattress. His fingers were digging into your ass and you were screaming into the pillow. This little rendezvous was impromptu after you had mentioned to Dean that Sam has the softest sheets in the whole bunker. You were playing beer bowling with the boys when Sam decided to go out for a run. He said he’d be back in a few hours and would bring back dinner. The small remark about the sheets inspired Dean to throw you over his shoulder as he always did when he was about to fuck you into oblivion. Yet instead of taking you into his room, he kick in Sam’s bedroom door and tossed you onto the bed._

_So there you were trapped under Dean’s strong body and on the edge of your third orgasm. Dean was groaning your name into your ear and then he stilled inside of you. He took a few deep breaths before flipping you over to your back. He rubbed his thumb over your sensitive clit and you bucked hips up. Your hands gripped the soft sheets and Dean pulled your legs over his shoulders when he leaned forward over you. His stiff cock slipped in easily and he filled you up perfectly, hitting every spot that your body craved. The thrusts were slow but precise. “Fuck… (Y/N). I can’t hold back any more… I’m gunna cum. Cum with me. I want to feel you cum around my hard cock.”_

_Dean paused when you both heard the front door slam and footsteps tumble down the stairs.  Sam got back from his work out and grocery shopping. You only had a minute before he would open the door and find you both. Dean wrapped his arm around your waist and picked you up. He stood up to the side of the bed, holding you up while he was still inside of you. The movement almost made you fall over the edge of bliss but you held back for sake of staying quiet. Dean quickly threw the blanket back into place and waddled over to the closet. He was able to get the door closed around 10 seconds before Sam walked into his room.  Your legs were wrapped around Dean’s waist and you leaned back against the wall of the closet to support some of your weight.  He had his hand covering your mouth and you could hear Sam walking around his room. Dean tightened his grip around your waist and he started to pump into you again. After a few more erratic thrusts, Dean shot hot streams into you while you followed behind in a few seconds later. He whispered sweet nothings into your ear as you came down from your high. The muscle convulsions took over your entire body and it took all of your effort not scream out._

* * *

This is the scene your mind decided to replay in the few seconds of awkward silence that sat between you and your best friend. Dean’s eyes were bloodshot and it looked like he hadn’t slept in weeks. You were trying to muster up the courage to speak first but every time you parted your lips, no words came out.

“Look… (Y/N)… I need to say something.” He was staring at his lap, avoiding eye contact.

“I get it. I screwed up and this needs to end. You don’t need to explain anything, Dean. We had a good run and I’m sorry I crossed the line. This is my fault. I’m making a choice to end it.”

* * *

_“Scared? Scared of what?” He was yelling. It made you cringe because you rarely saw Dean yell unless he was hunting._

_You spat words back. “Of losing you! You’re my best friend, Dean! And I fucked everything up! Distancing myself…pushing you away…it was easier than you telling me you didn’t want me around anymore. I could deal with myself making the choice, but not from hearing that from you.“_

_Dean walked over and cupped your face into his hands. You were surprise at how much you relaxed to his touch. You melted into his hands. You missed it. You missed him. ”(Y/N)… I already told you that we are in this together. We both made that mistake. We both need to clean it up. Together. “You fell forward onto his chest and began to cry. All of the sorrow, fear and regret was being let out and Dean was carrying you though it all. He hugged you tight and stroked your head. “We can get over this. We’ll be fine.”_

* * *

“What are you talking about?” He finally looks up at you with baffled eyes.

“Just don’t say you don’t want to be friends anymore. Okay? Because you and Sam… you guys are my family. I don’t have anyone else.”

“God, you are fucking unbelievable!” He stood up and walked across the room.

“Excuse me?”

“You can never give me one fuckin’ moment to say what I want. ‘nd you automatically fuckin’ assume that everything is your fault. Can you get it through you thick skull that maybe this could have been my fault? That maybe I am the one who took this too far? I mean I lo- you know what? It doesn’t matter. You’ve made it clear how you feel about all of this. I’m done.” He moved towards the door, too frustrated to keep talking with you.

“Dean…wait… please… don’t…don’t go… please.” Begging him to stay, you jump out of bed and grab his wrist. You couldn’t help but let tears stream down your face. The words hurt but you knew he was right. Your biggest fault was placing the blame on yourself when anything bad happens. He yanks his arm back, swings the door open and leaves. You followed him into his room and slammed the door behind you. After wiping the tears away with your sleeve, your gloom was over taken with anger. What gave him the right to get mad at you? You didn’t do anything wrong. He just said so himself. Who was he to talk for placing blame on themselves? “You have no right to just yell at me and then storm out! You owe me at least a tiny bit of respect and tell me what the hell is going on here. Call me crazy but I thought last night was incredible and then all of the sudden you are ignoring me and yelling at me? What the fuck is wrong with you? What the hell are you thinking? I’m not a mind reader! You’re supposed to be my best friend.”

“I can’t lose you!”

“Well clearly that isn’t true because you are pushing me away.”

“Don’t you get it, (Y/N)? I… can’t… lose… you. You are my Achilles’ Heel. My soft spot. I would do anything for you and if anyone against us that realized that, you’d be the biggest target out there. I didn’t think it was possible to care about you more than I already did… and then last night…” Dean sat down on his bed and covered his face with his hands. He was covering the shameful guilt that he was feeling. He knew he shouldn’t bee pushing you away. You already made that mistake and he knew that I didn’t work. “Don’t you see why this couldn’t happen? I won’t let you get hurt. I won’t let you live that kinda life. You deserve better than what I have to offer you. I’m poison. I’m a center for damage ‘nd everythin’ around me is destroyed. You deserve a good life… even if that means I’m out of the picture.”

His words made you livid. “That is not your choice! You don’t have the right to tell me what I do or don’t deserve.  This is my life.  You don’t get to decide whether someone is either good or poison to me. If I decide that something or someone in my life is worth the risk, then tough luck, Dean. My happiness is my choice! That belongs to me!” You finally sit down next to him on the bed and grab his hands. He looks up at you with puffy eyes and remorse. “And the same goes for you. You deserve to be happy, Dean. And no one but you can control that. If you want to be happy then be happy. But if you want to avoid the people that actually care about you and stay miserable… then that is something you chose and you can’t blame it one anyone except yourself. Happiness is something worth fighting for and frankly you don’t deserve whatever it is you’re pushing away if you aren’t willing to fight for it.” You give his hand a small squeeze and stand up to leave. “I understand why you’re scared. I do. So I’m making the final choice. End of the line. You’re off the hook.” You close the door behind you and start to cry again on your way back to your room.

You grab the biggest duffle bag you owned and started filling it with whatever clean clothes you could find. Living in the bunker with the Winchesters wasn’t going to work out anymore after this. You knew that living with them wasn’t going to last forever but this was the last reason you’d thought would be the reason for you to leave. A gust of wind blew through your hair and Castiel was standing next to you, folding a pile of clothes.

“What are you doing here, Cas?”

“I had a feeling you might need a hand.”

No matter hard you tried to hold back, your lip puckered and tears began to fall again. Sniffles and the ruffle of clothing was the only sound left in the room. Castiel only spoke when he asked if you’d like to pack up a certain item. After a few minutes the door swung open and Dean was standing at the entrance to your bedroom.

“Leave Castiel.”

“No, stay Cas.” You grabbed his hand before he could leave. “Don’t tell him what to do, Dean. He can stay if he wants. He’s my friend and he is helping me.” You continue stuffing clothes into your bag.

“I… um…” Castiel was conflicted. He knew his presence calmed you and he wanted to stay and be your support but Dean was radiating fury.

“We need talk about this, (Y/N).”

“There is nothing to talk about. It’s over. We knew the risks before we started this and now was are dealing with those consequences. So just… just leave me alone.” You walk over to your dresser and pull out a few things.

“(Y/N)…”

“Go away, Dean.” Dean was suddenly standing behind you and you could feel his breath on your neck. You turn around to face him with a stern look. You didn’t want to budge or give in but smell of leather and whiskey was pulling you in. His hands grabbed your face and he kissed you. You push him off of you and the slap him in the face. “You can’t just fucking kiss me and think that it’s going to make everything better.” He kisses you again but this time harder forcing you to push him off again. He goes in for a third time and you slap him again. Your breathing his heavy and labored and you want to scream at him but something comes over you and you jump into his arms, attaching your lips back to his. Dean is ravaging your mouth. He kisses you like it he couldn’t get enough of you. Devouring every single nip and savoring every lick. When you stop to look around the room, you notice that Cas had left. He must have felt uncomfortable at some point and gave you both some privacy.

Dean presses his forehead against yours with his eyes closed. He lets out a relieved sigh and pulls you in closer with his arms. “(Y/N)…”

“I know. You don’t have to say anything…”

“No… I need to say this. It’s important… (Y/N), you mean more to me than you will ever know. More than I ever thought it possible to feel for another person. Everything about you… The way you are effortlessly gorgeous without even knowing it. Especially when you are in sweats and one of my old tees. The way your eye brown quirks when you’re mad at me.” A tear was falling down your cheek and he rubbed it away with his thumb. “The way you way you pronounce the word espresso. The way you walk into a room ‘nd turn every head. The way you can handle a gun. The way you treat Sammy like family… ‘nd how you can out wit him with a single thought.” He presses a light kiss on the bridge of your nose. “The way your fingers feel on my skin.” He kisses on the corner of your eye. “The way you laugh at my ridiculous jokes.” Another kiss on the corner of your mouth. “The fact that you know every single lyric of all the songs I play in Baby.” Another kiss on your ear. “The smell of your shampoo and how it lingers on my pillow the next day. The fact that I am hard basically 24/7 when I am around you.” He pulls away a few inches so that he can look into your eyes. “I love you, (Y/N). I love that you make me feel important. You make me feel like life is worth living. You make me feel like I can make it in this cruel world ‘nd that there is light at the end of this God forsaken crap tunnel.” Tears were streaming down your face and you had a hard time seeing Dean through your blurry vision. He took the sleeve of his plaid button down and wiped your eyes. “I love you. And I am a fuckin’ idiot for almost letting you slip through my fingers.” You stand up on your toes and wrap your arms around his neck for support.  Dean bites the bottom of his mouth before you meticulously lock your lips onto his. All of the anger and vitriol disintegrated in that moment. Nothing felt more right than to be melting into your best friend’s arms.

“I love you too, Dean. I think I’ve always loved you… since the moment we met. I don’t know why it took me so long to realize it. We wasted so much time…”

“I know… but we don’t have to think about that. We’re here now ‘nd I love you. And nothing is ever going to change that.”

* * *

Later that night, Dean spent the night in you room. The sex was indescribable and you wish it never ended. Only thing left to do was to face the word head on. But getting out of bed was a challenge of it’s own. While you were getting dressed, you looked in the mirror and saw possessive marks all over your body. Your legs felt as if they could collapse at any moment from being sore and your neck was covered in hickeys.

“Geeze, babe. People might think a toothless vampire was trying to eat me or something.” Dean just chuckled in response and pulled the blanket over his head. “Oh no you don’t… you’ve gotta get dressed. If I can’t stay in bed today than neither can you.”

Dean let out an exhausted groan and sat up. “Fine…” He slipped on his boxers and picked up the rest of his clothes off of the floor. You heard the door close and you continued putting on your mascara. Dean tiptoed his way through the hallway as quietly as he could.

“Uh… Dean?”

“Shit.”

“So I uh… guess you and (Y/N) sorted things out then?” A big smile flew across Sam’s face.

“Shut up, Sammy.” Dean threw a shoe at his face and Sam dodged it by slapping it to the ground.

* * *

You were in the kitchen pouring yourself a cup of coffee when unexpectedly hands began to massage your shoulders. “Mmm… good morning.” His deep voice shook you to our core and sent a shiver down your spine. Dean kissed the temple of your head and then grabbed a mug. You moved across the room and leaned up against the table while you watched him take a sip of his drink. You placed your mug down when he walked over to you and gave him a wicked smile. “Really? Again? Even after last night?”

“What can I say, Winchester… I bounce back quickly.” Dean let out a sound that was half way between a growl and a laugh. He placed his mug down and attacked your lips. His rough movements and kisses caused your mug to fall off of the table and shatter into pieces. Neither of you broke away for the sound. Dean pushed into you harder and lifted you to sit on top of the table. He inched your skirt up and stood between your legs. Your tongue was exploring ever inch of his hot mouth when his fingers ran through your wet folds. You let out a sweet moan and lean back to give him better access. You hand moved to grip the table and you knocked Dean’s mug to the ground. The mug shattered and coffee was splattered all over the floor. Dean’s thumb was rubbing against your swollen clit when suddenly Sam burst into the kitchen with a gun.

“Oh my God…. gross. What the fuck you guys? Uhg. On the table where we eat? Really?”

“Geez, Sammy? Can’t anyone here get some privacy?”

“Just because I know about this now doesn’t mean I want a free show. You’re in the fucking kitchen, Dean. And I heard a loud shatter. I thought (Y/N) was in trouble.”

“Trust me, she’s in good hands.” Dean returned to kissing you and your hands thread through his hair after Sam left with a loud scoff.


End file.
